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Mechanistic insight into palladium-catalyzed cycloisomerization: a combined experimental and theoretical study

Abstract:

The cycloisomerization of enynes catalyzed by Pd(OAc)2 and bis-benzylidene ethylenediamine (bbeda) is a landmark methodology in transition-metal-catalyzed cycloisomerization. However, the mechanistic pathway by which this reaction proceeds has remained unclear for several decades. Here we describe mechanistic investigations into this reaction using enynamides, which deliver azacycles with high regio- and stereocontrol. Extensive (1)H NMR spectroscopic studies and isotope effects support a pal...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's version

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Publisher copy:
10.1021/jacs.7b05436

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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Walker, PR More by this author
Couce-Rios, A More by this author
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Department:
Oxford, MPLS, Chemistry
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Funding agency for:
Mekareeya, A
Publisher:
American Chemical Society Publisher's website
Journal:
Journal of the American Chemical Society Journal website
Volume:
139
Issue:
29
Pages:
10104–10114
Publication date:
2017-07-12
Acceptance date:
2017-06-29
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Pubs id:
pubs:708017
URN:
uri:cb2f68e8-355a-45d4-b2d1-9d18badb6a04
UUID:
uuid:cb2f68e8-355a-45d4-b2d1-9d18badb6a04
Local pid:
pubs:708017
Language:
English
Keywords:

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